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1,3,4-thiadiazole fluorouracil compound as well as preparation method and application thereof

A technology of compound and alkyl, which is applied in the field of pesticides, can solve the problems of increased risk and increased resistance of pests, and achieves the effects of low cost, overcoming the problem of drug resistance, and simple synthesis process

Inactive Publication Date: 2010-06-09
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

What is certain is that if imidacloprid is used continuously and in large quantities, the resistance level of crop pests such as aphids will inevitably rise further, and the risk will inevitably increase

Method used

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  • 1,3,4-thiadiazole fluorouracil compound as well as preparation method and application thereof
  • 1,3,4-thiadiazole fluorouracil compound as well as preparation method and application thereof
  • 1,3,4-thiadiazole fluorouracil compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] This example illustrates the synthesis of 2-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide

[0061] Into a 250ml four-neck flask, add 0.01mol of 2-amino-5-phenyl-1,3,4-thiadiazole, 100ml of acetone, and 0.02mol of anhydrous potassium carbonate. 0.02mol of chloroacetyl chloride dissolved in 15ml of acetone was added dropwise under ice-cooling. After the dropwise addition was completed, the mixture was reacted at 20°C for 4 hours and filtered. The filter cake was acid-washed with 1mol / L HCl solution, 5% NaHCO 3 The solution was washed with alkali and washed with water to obtain a crude product. The product is obtained by recrystallization from ethanol, melting point: 220-223°C.

Embodiment 2

[0063] This example illustrates the synthesis of 2-(5-fluorouracil-1-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide.

[0064] Add 0.006mol of KOH, 15ml of water, and 0.005mol of 5-FU into a 100ml four-neck flask. The pH value of the solution was adjusted to 10 at 20°C, and 15 ml of a DMF solution containing 0.0036 mol of 2-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide was slowly added dropwise. After the dropwise addition, the temperature was raised to 120° C. for 3 hours to react. After cooling down to room temperature, a solid precipitated out and was filtered, and the crude product was recrystallized from DMF. A white flocculent solid was obtained. Yield 82%. Melting point: >300°C

[0065] 1 H NMR: 4.60(2H, s), 7.53(4H, s), 7.93~8.30(2H, m), 11.96(1H, s), 13.06(1H, s)

Embodiment 3

[0067] This example illustrates the synthesis of 2-chloro-N-[5-(3-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide

[0068] According to the method of Example 1, in a 250ml four-necked flask, add 2-amino-5-(3-methoxyphenyl)-1,3,4-thiadiazole 0.01mol, acetone 100ml, anhydrous potassium carbonate 0.02 mol. 0.02mol of chloroacetyl chloride dissolved in 15ml of acetone was added dropwise under ice-cooling. After the dropwise addition was completed, the mixture was reacted at 20°C for 3 hours and filtered. The filter cake was acid-washed with 1mol / L HCl solution, 5% NaHCO 3 The solution was washed with alkali and washed with water to obtain a crude product. The product is obtained by recrystallization with ethanol, melting point: 228-232°C.

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Abstract

The invention discloses a 1,3,4-thiadiazole fluorouracil compound as well as a preparation method and application thereof. The compound has a general formula I, wherein R is substituted phenyl, aromatic heterocycle or aryloxy alkyl; the substituent group R1 in tri-substituted phenyl is hydrogen, nitryl, alkoxyl, halogen atom, alkyl, substituted alkyl or phenoxyl, R2 is hydrogen, nitryl, alkoxyl, halogen atom, alkyl, substituted alkyl or phenoxyl, and R3 is hydrogen, nitryl, alkoxyl, halogen atom, alkyl, substituted alkyl or phenoxyl; and the aromatic heterocycle is pyridine, thiofuran, furan, indole or isoindole. The invention has less compound consumption, good insecticidal effect, simple process method, low cost and wide market prospect.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a 1,3,4-thiadiazolylfluorouracil compound, a preparation method thereof and an application as an insecticide. The process method of the invention is simple, the insecticidal effect is good, and the market prospect is broad. Background technique [0002] my country is a big agricultural country, and it is also one of the big countries that produce and consume pesticides. According to statistics, from planting to storage, due to the harm of diseases, insects, weeds and rats, at least 10%-15% of grain is lost, about 15% of cotton is lost, and about 20% of fruits and vegetables are lost, and the use of pesticides can restore most of the losses above. But at the same time, due to the large-scale use of pesticides and the supervision and management lagging behind the production, it has caused pollution to the ecological environment and harm to human health. The development of h...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D417/14A01N43/824A01P7/04A01P7/02
CPCA01N43/82
Inventor 万嵘王锦堂王朋韩锋王瑶于鹏何秋张建强
Owner NANJING UNIV OF TECH
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